


How To Succeed In Business Without Really Trying

by MerWorldProblems



Category: Marvel Cinematic Universe, Spider-Man: Homecoming (2017)
Genre: Challenge Response, Escort Challenge, Escort Service, Hero Worship, Loss of Virginity, M/M, Morally Ambiguous Steve Rogers, Peter is Legal, Virginity Kink
Language: English
Status: Completed
Published: 2018-06-06
Updated: 2018-06-06
Packaged: 2019-05-18 23:37:32
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,908
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14862476
Author URL: https://archiveofourown.org/users/MerWorldProblems/pseuds/MerWorldProblems
Summary: Written for the Starker Escort Challenge on Tumblr.Tony Stark liked to think he was a smart businessman. That is except for when he needs to outdo his former associate Steve Rogers in the dick-measuring contest of entrepreneurship. When Steve drops his new business venture, one wide-eyed and innocent Peter Parker, into Tony's lap, well, how can he say no to that?





	How To Succeed In Business Without Really Trying

The call from his old associate Steve Rogers seemed to come from nowhere. Radio silence for years and now Steve just called Tony up for a drink, mentioning that he wanted to propose something to him.

He and Steve went way back, having met in college and worked together on a few...top-secret projects. Apparently Steve was Big News in the American government but Tony could never know why exactly.

He didn't think it within his best interest to pry.

Tony put on his best attire because he just had to impress the guy, despite not having heard from him in years. Steve knew Tony was wildly successful in his career but he still couldn't let that need to impress go.

He looked at himself in the mirror, sliding on his tinted aviators because they just seemed to complete his whole look. A bit of slicking back of his hair and he was set, looking literally like a million bucks.

He made his way to the ground floor and took his spot in the limo. The chauffeur knew where to go. During the drive, he googled Steve Rogers' online presence, finding his Linkedin and Facebook for the most part. The results were disappointing. Tony hoped to have something to refer to when they meet up. That’s what happens when his whole career is shrouded in mystery. Guess it's just small talk for now. Great.

They pulled up to the snazzy Manhattan bar Steve invited him to, and fortunately the paps were sparse. Tony likes to think that's Steve's doing, somehow.

The hostess was a ridiculously attractive woman, likely an aspiring model. New York for you. She had obviously been expecting him and brought him over to Steve’s table.

"Growing your beard out?" Tony said, taking the seat next to him. Tony noticed Steve's new look, perfectly combed back hair and a new beard growing in. Looked good, a little too good, as always.

"Trying something a little new." Steve nodded and grinned at him in his stupidly charming way. Tony tried not to let it irritate him. "Good to see you bro. You're looking fancy as ever."

"Oh this old thing? It was laundry day." Tony just shrugs. Steve doesn't appear to be buying his nonchalance, not that he cares.

"What do you want? I'll buy the first round. Gin and tonic?"

"Precisely."

"Done." Steve made a hand gesture to the server, pointing to Tony like there was some unspoken agreement.

Tony's eyebrows raised. Alright then. Steve was definitely up to something. "You look good. Love the glasses."

"Well I appreciate the compliment." Tony said, when the gin and tonic materialized in front of him.

"Anything else I can get you, Mr. Stark?" The waitress said. Tony never got used to having strangers know who he is.

"No, thank you." He said, shooing her away. He sipped the drink, it was...perfect. Right amount of lemon juice to offset the bitterness. Perfect. Yeah, Steve was definitely plotting something here, Tony is so eager to find out what’s going on.

Tony and Steve shoot the breeze for a while, comparing dick sizes....er, comparing successes and Tony was feeling buzzed and relaxed.

"Now Steve...if we're done flirting now. What's this proposal that you've been hinting about?"

Steve's grin widened, but his poker face never faltered. "I'm looking for potential clients."

"Just be honest, you need an investor." Tony knew how this works.

"Not necessarily an investor, no. I have some boys."

"Boys? What interest would I have in boys?"

"Oh they're all legal age, I assure you."

It dawned on Tony what he means. "Oh...so you're what, running an escort service now?. What makes you think I'd have any interest in this?" Tony said. Of course he was interested, but he didn't want Steve to have the upper hand here.

"A unique young man just signed up. A virgin, just dying to lose it. To a certain mogul named Tony Stark. His childhood crush."

Jesus fuck, did Steve know his audience, that sales pitch, well, it wasn’t something Tony could pass up.

"He's a virgin...and he wants me?" Tony tried his best to seem disinterested...it wasn't working.

"Interested?"

Tony said nothing. He, fuck, he needed a drink...and so he gestured to the waitress again. Steve was grinning so hard Tony wanted to punch out his stupid white teeth. Why does he have to be such a perfect jackass all the time? It was ridiculous how quickly the drink was ready for him. Good.

"How bout I leave you my card here..." Steve slid his business card into Tony's view. "I'll reserve the boy for you...for a time. But this kid is desperate for money, and he won’t be able to hold onto his virginity for much longer." Steve smiled at him, nodding, holding his hands out. Tony hated how charming he was.

Tony also just hated how tempted he was by this. Damn...a fresh face boy, completely untouched worshiping him.

"He's a beautiful baby-faced twink, 22 years old but looks 16." Steve pulled up a picture on his phone, a smiling kid with a ridiculously toned body, standing shirtless and gazing wide-eyed up into the camera lense. "I can't get him to stop smiling. I wanted an enticing pout but he couldn't stop laughing. Oh well, right?"

"Fine...I surrender. How much?"

"One million."

"Psh. I make that in an hour." Tony said, needing to be competitive. It was definitely a lot of money, but he needed to show up Steve, against his better judgment. And hey...it's not like he isn't tempted. It's a large chunk of his wealth, but it wouldn't be putting him in the red by any measure.

"Can we shake on it then?"

Tony was hesitant...but he just shook on it. Dammit, his need to show up Steve Rogers was gonna kill him.

"The kid better be worth it."

"Oh you'll enjoy it, I assure you. We can discuss his scheduling..."

And Tony had an expensive virgin escort coming by next weekend, and Steve covered his two gin and tonics. Or might have been three. He can't remember at this point.

Wouldn't be the first time he hired an escort, just...not one this expensive.

Fuck it. He's buzzed and he's going to enjoy it.

\--

Today's the day, and it's been a long work week. Tony can hardly wait for the the boy to come by tonight, having the penthouse get ready for his arrival. The minibar is stocked, the bed was ready and made...and he planned to get this kid drunk.

He’s not a kid...he's supposedly 22, Tony reminds himself, perfect legal, except for the prostitution angle Oh well, not the first time he’s been on the shadier side of the law, and likely not the last.

Tony arranged for his most trusted advisor to ensure the boy arrives with ample discretion. The "cover" story was an internship interview. Tony didn't think anybody bought that, an interview on a Saturday night? Oh well. He didn't think it through...as he usually doesn't think things through.

And the signal came up. He was here. The elevator door opened to reveal the same boy that Steve had shown him. Jesus...

"Hey there."

"Hi...I'm Peter."

"Hello Peter. I'm Tony Stark. Welcome to my humble abode." Tony held his hands out, proud of his quarters.

Peter appeared extremely nervous, looking around the penthouse and his breath seemed to be shortening. "I can't believe I'm here..."

"I hear you were interested in having me hire you."

Peter's eyes widened, and he seemed a little embarrassed. "Um, yeah...um Steve Rogers made a pretty convincing case. He seemed confident he could get you to hire me."

"He's a ridiculously good salesman. Don't know how I never snatched him up." Tony fixed his drink at the minibar, gin and tonic. "Could I make you something?"

"Um, yes, please. Whatever you're having." Peter stepped into the middle of the penthouse common area, sitting down on the couch.

Tony handed him the fixed drink, seating himself next to Peter. He watched Peter drink and grimace at the taste. Such innocence. Peter continued to drink it, probably not wanting to waste Tony's booze. Which was a bit ridiculous since Tony was paying an arm and a leg for the kid.

"Look Peter, if you don't like, don't drink it."

"O-oh, I know. I just want to be..."

"Drunker? Got it. Don't be nervous. It's just me." Tony held his arms up in a shrug. Peter clearly was not comforted by that. Damned if Tony didn't find that a little arousing. Tony was clearly going to hell.

"So Peter...is this really your first time?"

Peter just nodded, eyes wide. "Yeah...it is."

"Never....done anything? Had your cock sucked maybe?"

"No. Nothing."

"Huh, 22 year old guy, very attractive, muscular. Hard to believe."

"It's true...I'm not really sure why not. I just...haven't had the opportunity I suppose."

"Well, I'll make sure you enjoy this." Tony's voiced dropped, as he stroked Peter's cheek whose lips parted in a gasp. "Don't be so nervous."

"I just hope I'll be worth the money."

"The second you walked in, it was worth the money."

Peter rolled his eyes in a laugh. "Cheesy." He laughed for a moment, before the nerves seemed to overtake him again.

"I'd like to help you relax." Tony said, pushing Peter to lie back on the couch. He rested his head against the cushioned armrest, but his body still felt stiff. Tony was going to do his best to relax him.

He pulled his sweater above his head, studying the toned skin beneath. He was...perfect. "God what are you? An Olympian?"

"Gymnast and dancer...actually."

"No wonder you were so pricey." Tony climbed over him kissing Peter's neck.

"Oh that feels good..." Peter breathed pressing his head back.

Tony's mouth was pressed on the boy's skin, nipping at the skin, rubbing his arm in an attempt to relax him. Tony could feel his tense muscles begin to relax, and Peter made light whimpering noises at his light ministrations. Tony could tell Peter was going to be...sensitive. And responsive. He's barely touching him at this point.

Tony unzipped Peter's jeans, but he didn't want to pull his cock out yet. He gently pressed his hand inside his boxers, lightly touching the cock inside. He was so hard, and the whimpering didn't stop. In fact, it was intensifying. It was stirring his own cock up...Tony's jeans starting to tighten.

"Do you like it? Having me be the first person to touch you here?"

"M-Mr. Stark..." Tony's words clearly weren't helping him. Peter seemed to be gripping the cushions and he seemed like he was going to come way too quick.

"You're so close already, aren't you?"

Peter was gasping hard, gripping Tony's shoulders, when his whole body shuddered and trembled. "No no no..." The mess under his plaid boxers became apparent. "I...I didn't want it to happen so soon...I'm so sorry Mr.Stark!"

Tony clearly was not going to last long either. "Don't. Please. You look really beautiful when you come...and I'm planning to make it happen again..." Tony stroked his cock again, causing a jerk in the young boy's body as he was clearly still sensitive. "...And again..." Tony gripped him and made a rough stroke. He continued doing that until Peter begged him to stop.

"Please...stop please!" Peter whined, after it seemed like each touch of Tony's fingers was making him shudder and whine.

"Did you think you'd be begging me to stop touching you?" Tony laughed. Peter was laughing too, amidst his heavy breathing.

"Doing ok?" Tony said, stroking the young boy's cheek in an act of tenderness. Peter was looking up at him with the most trusting, innocent eyes that Tony almost felt guilty. Although not a million dollars worth of guilt.

"Just nervous..."

"Why don't we go take a bath. Maybe that'll help you relax."

"That sounds really good actually." It seemed like Peter visibly relaxed.

Tony drew the bath in his lavish bathroom, in the huge garden tub that could fit two, maybe even three of him comfortably. Peter followed behind him, beginning to undress down to his boxers. That's right...he's still sitting in his come. He seemed hesitant to take it off, clearly self-conscious.

The bath was filling up, Tony pouring soap under the faucet to form bubbles.

Peter watched him, putting off his inevitable nudity. "Bubble bath?"

"Yes. THE Tony Stark likes bubble baths...escort-client confidentiality is a thing, right?"

Peter nodded, amused. God he was cute. "So Peter...you gonna take a bath in your messy boxers there? Take it off." Tony demanded, despite the fact that he's still fully dressed. He wanted Peter naked before he got naked himself.

Peter nodded, nerves returning to his features. "Okay..." Peter pulled them down. He stared at the floor, grasping his bicep in an act of self-comfort.

Tony stood in front of him, still fully clothed, just mapping his body, the grooves of muscle. "Get in. The water is perfect." Tony's voice dropped low, as Peter looked up at him with those wide nervous eyes again. He obeyed the command, sighing as the warm water enveloped him.

Tony finally began to undress, the clothes getting a little constricting to his heightened senses. Peter watched him undress, and Tony...enjoyed being watched. Peter's expression was full of wonder and awe, and damn if Tony wasn't kind of enjoying putting on this show. The kid was worshiping him with his eyes, and it's clear this is something he's been fantasizing about for a long time...

Goddamn that's arousing.

"Scooch." Tony said, motioning for Peter to make space for him to take his seat behind him. "Come on, lay back against me...that's it." Peter's warm body laid back against his, head rested on his shoulder. Tony relaxed him by rubbing his shoulders, running his hands over his body gently, and Peter was in heaven. His head rolled to face Tony, lips parted and eyes hooded.

Tony kissed him. It was chaste and meant nothing, but the moment was there. Tony had to seize the moment.

Peter snapped out of his trance at that, kissing him back. That was when he started going for it, deepening the kiss. The quiet of the bathroom with the only sounds being the movement of water, there was an electricity in the air, and it seemed Peter was starting to find his element. He was getting braver in going for the touches now, turning over to press against him, rubbing their cocks together under the water. It was so good...Tony moaned against the boy's mouth and pressing his hands against his back. He encouraged him to push forward and roll his hips, eliciting a long groan from Tony's throat.

"Y-you think you're ready for the bed now kid?"

"Yes Mr. Stark...I-I want you so bad. I want you inside me...I've wanted it for as long as I can remember..."

"Well we can certainly arrange all of that..." Tony grinned, moaning as his hand found Peter's hair and massaged his scalp. Peter's face was buried in Tony's shoulder. He could feel his quickening hot breath. Tony's pleasure built and he knew he had to put a stop to this..."Ok..bedroom now." It took every ounce of Tony’s mental and physical strength to stop Peter and push him off

"Right, bedroom." Peter repeated.

Tony climbed out of the bath wrapping him and Peter up in towels to dry off. "God I want you so bad Peter..."

The bed was made flawlessly, unsuspecting of the debauchery it would soon be witness to. Tony sat on the edge, Peter pressed between his legs. They grinned at each other like idiots. There was too much worship going on right now, Tony's cock aching for stimulation again.

"You want to...suck it?" Tony said.

"Y-yeah. I'll do that."

"Oh yes...please do..." Tony massaged at Peter's scalp, groaning just in the anticipation as his head lowered, closer and closer, Peter now on his knees in front of him.

"Just let me know if I do it wrong...ok?" Peter said nervously, staring at Tony's cock right in front of his face. He made a few experimental licks at the tip, causing Tony to sigh and loll his head back.

"Wrap your mouth around the tip...don't go too deep right away. Just uh--ohh....ok..." Tony was interrupted when Peter did as instructed, felt good...he was rendered momentarily speechless when he felt Peter's tongue swirling his tip and dipping his slit. "Oh...you're a natural..."

He looked at Peter's face who was looking back up at him every so often, enjoying the encouragement.

"Feels...really good..try going a bit deeper baby, as far as you can...yes....ohhhhhhhh..." Peter did just that as well when Tony felt his tip hit the back of his throat. Peter choked and gagged, Tony's cock falling out of his mouth. He coughed a bit to gain his bearing back. "It's okay baby...you did good...really good..." Tony recovering his breath back. He pulled Peter to face him again. "I think you're ready to get fucked now...what do you think about that?"

"I really...I want you to fuck me. I'm ready for it."

"You're gonna fucking kill me kid, you know that?" And with one fell swoop Tony had Peter pinned to the bed beneath him. His mouth was at Peter's neck again, kissing under his ear. The lube was available next to the bed, Tony had it ready earlier. "I've been thinking about this ass all night." Tony said, kneeling and spreading the boy's legs wide. He held one leg over his shoulder, his lubed finger pressed to his asshole. Peter's body jerked at the touch.

"How does it feel to have me touching you...where nobody else has ever touched you?"

"It's...amazing...please..."

Tony pressed his finger inside. Peter's begging was not going to get old, he foresees. He momentarily wonders if Peter would prefer this to be a one-time thing...Tony finds himself hoping not. He'll just think about that later.

For now he's just going to indulge in the delicious whimpers that keep falling out of Peter's throat the deeper he goes inside him, and this was just with his fingers. He had two fingers scissoring him open causing Peter to grip the sheets hard, driven mad by the unfamiliar but pleasurable sensations brought on by Tony's finger tips.

Peter became frantic. "Please do it now."

"You asked for it." Tony grinned. He kept Peter's leg on his shoulder and pressed down on him, pressing their foreheads together now. He finally pressed inside him pressing slowly...maddeningly slow. Tony groaned long when he was fully sheathed.

Peter gripped his shoulders, his face grimaced and he groaned. He sounded in pain.

"How does it feel?"

"Weird...but don't stop please?"

"Never." Tony just stayed like that until he felt Peter relax around him and stop grimacing.

"Okay...do it. I'm ready."

"Oh thank god..." Tony gasped. His hips moved inside Peter, and he began a slow rolling movement inside him.

Peter was so responsive. At each hip roll, Peter moaned and gasped, and the grip on Tony's shoulders was tightening. Tony took it as encouragement. And just god he felt warm and wet and so amazing...Tony couldn't take it anymore, he needed more. He thrusted harder experimentally, warranting a high pitched cry from Peter's throat. It was the most glorious sound...

Tony wanted to keep pulling those noises out of him, hitting a spot inside him that made Peter tremble and gasp even harder.

"Yes...there it is." Tony said, continuing his rhythm. Peter wrapped his other leg around Tony's waist, encouraging his thrusts inside him. Peter's breathing was coming out increasingly labored, coming out in rhythm with the increasing speed of Tony's thrusts.

It wouldn't be long now, Peter was completely lost in it with his eyes pressed shut, mouth wide open, moans growing even more high pitched. The grip on his shoulders was tightened when he felt Peter stiffen and shudder, feeling the wetness of his orgasm hit his belly a moment later. He watched Peter's face as his mouth fell open carefully through his orgasm. "Fucking gorgeous..." Tony breathed between his own moans, feeling his orgasm building rapidly. His moans turned into shouts when he felt his body surrender to it, the warmth around his cock becoming too much to bear. He came inside him, trembling, and looked down at his asshole leaking his come. It was a beautiful sight...just perfect.

He sighed hard, body collapsing on the bed right next to Peter. He was on his back staring up at the ceiling, completely blissed out. Wow...he needed that bad.

A few moments later once he recovered, he looked at Peter next to him. He appeared...sad somehow. Tony once again felt that familiar 'almost guilt' that was threatening him earlier, and he worried Peter was regretting this. He wondered why he needed the cash so bad.

"How did it go?"

"Amazing..." Peter grinned wide. Still, the sadness was gripping at the hinges of his expression, his grin faltering after a moment.

"But?" Tony pried.

"But it's just...well it's over now."

"What makes you think it's over? I paid a pretty penny for you."

"I mean tonight, isn't this just a one-time thing for you? You probably won't want to see me again. I’m nobody! And you’re, well, you!”

"Oh...I don’t know about that. I could see myself keeping you around, keep your income flowing...providing you supply the goods." Tony half-grinned at him.

Peter seemed legitimately surprised at the offer. Tony wondered what made this kid feel so undesirable. If Steve made him feel that way...he was gonna kick in those stupid perfect teeth of his. "A-are you sure?"

"Of course I'm sure. I'm thinking I don't want to share you with anyone else." Tony grasped Peter's jaw. "And I was told you needed money bad. I’ll double whatever Steve is paying you. “

Peter’s eyes widened. “What, you’re sure? I can’t possibly be worth that much to you.”

“Absolutely sure. And either you can be treated like shit by strangers every night, or you can get paid to get fucked by the same man, you know, me. I’ve heard of worse ways to make extra cash.”

Peter nodded, looking overwhelmed. “Um..right Mr. Stark. That sounds...that would just be perfect.”

Peter looked like he was on the verge of tears, and it made Tony...curious. He turned to his side and wrapped one arm around Peter to comfort him. He didn’t know where this tenderness came from but he felt something for the kid. Something he can’t explain.

“Hey, don’t worry about it. Whatever it is…I can fix it. Just name it.”

Peter looked up at him with wide, sad eyes and Tony wondered who hurt this kid. He’d kill them. 

“I’ll do it. I’ll take your offer.” Peter finally said. 

“Splendid.” Tony kissed his forehead. Peter’s expression turned to relief, tinged with apprehension. “And don’t worry about Steve. I’ll take care of him. Besides, we’ve still got all night…”


End file.
